WO2025196161A2 - Compositions cosmétiques, leur utilisation et procédés d'utilisation de telles compositions - Google Patents

Compositions cosmétiques, leur utilisation et procédés d'utilisation de telles compositions

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Publication number
WO2025196161A2
WO2025196161A2 PCT/EP2025/057575 EP2025057575W WO2025196161A2 WO 2025196161 A2 WO2025196161 A2 WO 2025196161A2 EP 2025057575 W EP2025057575 W EP 2025057575W WO 2025196161 A2 WO2025196161 A2 WO 2025196161A2
Authority
WO
WIPO (PCT)
Prior art keywords
oil
acid
composition
vegetable
polyester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/057575
Other languages
English (en)
Other versions
WO2025196161A3 (fr
Inventor
Konstantin Nikolaev GOLEMANOV
Pierre-Emmanuel Dufils
Silvia Helena GUERRA DOS SANTOS
Vincent MIRALLES
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Quimicos E Solucoes Sustentaveis Do Brasil SA
Specialty Operations France SAS
Original Assignee
Quimicos E Solucoes Sustentaveis Do Brasil SA
Specialty Operations France SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Quimicos E Solucoes Sustentaveis Do Brasil SA, Specialty Operations France SAS filed Critical Quimicos E Solucoes Sustentaveis Do Brasil SA
Publication of WO2025196161A2 publication Critical patent/WO2025196161A2/fr
Publication of WO2025196161A3 publication Critical patent/WO2025196161A3/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

Definitions

  • the present invention relates to cosmetic compositions.
  • the present invention relates to hair care or skincare compositions as well as use and methods for using such compositions.
  • the present invention relates to haircare or hair conditioning compositions based on vegetable oils and a co-active substance.
  • the present invention also relates to compositions which are effective for skincare, for example as emollients, skin repair creams, moisturizing creams and ointments, and related products.
  • the present invention relates to hair care compositions exhibiting both conditioning and cleansing properties for the simultaneous washing and conditioning of the hair.
  • shampoo compositions based essentially on conventional surface-active agents of, in particular, anionic, non-ionic and/or amphoteric type, are used for washing the hair.
  • compositions are applied to wet hair and the foam generated by massaging or rubbing with the hands makes it possible, after rinsing with water, to remove dirt initially present on the hair.
  • these base compositions possess cosmetic properties that remain fairly weak, in particular as the relatively aggressive nature of such a cleansing treatment can result, in the long term, in more or less marked damage to the hair, damage related in particular to the gradual removal of the lipids or proteins present in or at the surface of the hair.
  • conditioners or conditioning agents which are intended mainly to repair or limit the harmful or undesirable effects brought about by the various treatments or attacks to which keratinous materials are more or less repeatedly subjected.
  • conditioners can also improve the cosmetic behavior of the keratinous materials.
  • conditioning agents especially in hair care formulations, are cationic polymers, cationic surfactants, silicones and/or silicone derivatives.
  • cationic polymers cationic surfactants
  • silicones cationic surfactants
  • silicone derivatives silicone derivatives
  • Another object of the present invention is to provide skin care and hair care compositions, for example, hair or skin cleansing and conditioning compositions.
  • Another object of the invention is to provide hair care compositions which exhibit good conditioning properties, such as ease of detangling, softness and shine properties, and a satisfactory viscosity.
  • the present invention also relates to use of the cosmetic compositions as well as to a method for preparing a chemically modified vegetable oil, which can be used in the aforementioned cosmetic compositions, and to a chemically modified vegetable oil obtained by said process.
  • a compound means one compound or more than one compound.
  • the term “average” refers to number average unless indicated otherwise.
  • % by weight As used herein, the terms “% by weight”, “wt.-%”, “weight percentage”, or “percentage by weight” are used interchangeably. The same applies to the terms “% by volume”, “vol.- %”, “vol. percentage”, or “percentage by volume”, or “% by mol”, “mol- %”, “mol percentage”, or “percentage by mol”.
  • endpoints includes all integer numbers and, where appropriate, fractions subsumed within that range (e.g. 1 to 5 can include 1, 2, 3, 4 when referring to, for example, a number of elements, and can also include 1.5, 2, 2.75 and 3.80, when referring to, for example, measurements).
  • the recitation of end points also includes the end point values themselves (e.g. from 1.0 to 5.0 includes both 1.0 and 5.0). Any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • the term “about” or “approximately” means an acceptable error for a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined. In certain embodiments, the term “about” or “approximately” means within 1, 2, 3, or 4 standard deviations. In certain embodiments, the term “about” or “approximately” means within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%), 1%), 0.5%), or 0.05%) of a given value or range.
  • any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • a range of " 1 to 10" is intended to include all sub-ranges between and including the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.
  • a cosmetic composition containing a particular combination of a vegetable oil and a chemically modified oil compound makes it possible to achieve the objective as outlined above.
  • the specific combination of a vegetable oil and a coactive substance in the cosmetic compositions of the invention has synergistic activity in terms of beneficial effects for haircare and skincare.
  • the cosmetic compositions of the invention may provide a synergistic effect due to the particular combination of the oil and co-active substance with respect to in vivo/invitro sensorial performance, deposition of active, hydrophobization of the hair fiber, and/or spreading on the surface.
  • compositions of the invention can show increased performance in combing tests (in vivo tests), deposition of conditioning substances on hair fibers, and/or hydrophobization of the fibers by the composition (as measured via the contact angle).
  • cosmetic compositions which are essentially free of silicone oil.
  • Figure 1 shows measurement results for determining the contact angle of a composition of the present invention.
  • the invention provides cosmetic compositions which comprise (A) one or more vegetable oil(s) and (B) one or more co-active substance(s), wherein the co-active substance (B) is one or more chemically modified oil, selected from the group, consisting of (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.
  • the (i) oil oligomers derived from triglycerides or liquid esters shall refer to the oligomers resulting from the reaction between a triglyceride or a liquid ester with one or more monofunctional fatty acid.
  • the molecule obtained corresponds to the starting triglyceride or to the liquid ester grafted with one or more fatty acids, as illustrated below:
  • the (ii) oil-based estolides derived from triglycerides or liquid esters shall refer to the oil-based estolides resulting from the reaction between triglycerides or liquid esters with one or more molecules carrying at least two carboxylic acids.
  • the molecule obtained corresponds to the condensation of the triglycerides or liquid esters via the difunctional molecules, as illustrated below:
  • the present invention provides skincare and haircare compositions comprising a mixture of (A) one or more vegetable oil(s) and (B) one or more coactive substance(s), wherein the co-active substance (B) is as defined above, as well as several aspects of use for said cosmetic composition.
  • the composition comprises a vegetable oil.
  • the vegetable oil is one or more, selected from the group, consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil, Baobab oil, Rose flower oil, Corngerm oil, Walnut seed oil, Canola (Rapeseed) oil, Brazil nut oil, Baobab seed oil, Moringa Oleifera Seed oil, Camelina sativa seed oil, Babassu nut oil, Camellia oil, Macadamia Integrifolia S.
  • the vegetable oil (A) can comprise(s) one or more of monoglycerides, diglycerides, triglycerides, mixtures of mono- di- and triglycerides, and/or liquid esters.
  • the above vegetable oils can be used as a mixture of monoglycerides, diglycerides, triglycerides, mixtures of mono- di- and triglycerides.
  • Many vegetable oils comprise a major content of triglycerides. It is also possible to chemically modify the triglyceride content and to increase the diglyceride content by means of the method described in the Experimental section below.
  • the vegetable oils can be used as supplied or after modification by means of glycerolysis as described below in the Examples Section.
  • the composition of the invention also comprises a co-active substance or coactive ingredient.
  • the co-active substance (B) is a chemically modified oil.
  • the co-active substance can be (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.
  • the aforementioned composition preferably comprises one or more co-active substances, selected from the group, consisting of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/dicarboxylic acid copolymer (and) Cs-Cw carboxylic acid.
  • co-active substances selected from the group, consisting of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/dicarboxylic acid copolymer (and) Cs-Cw carboxylic acid.
  • the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Jojoba oil, Cassia oil, Argan oil, coconut oil, Rice Bran oil, and Crambe oil, more preferably from the group consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil.
  • the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Guar oil, Amaranthus oil, Baobab oil, and wherein the co-active substance (B) is one or more, selected from (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.
  • the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and coconut oil, and wherein the co-active substance (B) is one or more, selected from (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.
  • the co-active substance can be selected from dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and C8-C14 carboxylic acid.
  • the co-active substance (B) is selected from the group, consisting of Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride.
  • the oil-based estolides (ii) are preferably derived from vegetable oil triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms.
  • the oil based estolides (ii) are derived from Lauric acid and epoxidized triglycerides polyester, lauric acid and epoxidized jojoba oil polyester, hexanoic acid and epoxidized triglycerides polyester, hexanoic acid and epoxidized jojoba oil polyester, and hexanoic acid and epoxidized jojoba oil polyester.
  • the vegetable oil is one or more, selected from the group, consisting of avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil, more preferably from the group consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil.
  • the weight ratio of the vegetable oil (A) to the co- active substance (B) can be 40:60 to 70:30, preferably 50:50.
  • the present invention also provides skincare or haircare compositions, comprising the cosmetic composition as defined herein.
  • composition preferably further comprises one or more ingredients, selected from the group, consisting of a pH regulating system, emollient(s), excipient(s), a surfactant system, guar, rheology modifier(s), antioxidant(s), conditioning polymer(s) and solubilization agent(s), said composition preferably comprising citric acid in a pH regulating system, said composition more preferably comprising cationic/non cationic surfactant(s) in an amont from 10% to 25% by weight, based on 100% total weight of the composition.
  • composition preferably further comprises a sulfated or non-sulfated chassis.
  • the aforementioned composition has a silicone oil content of 0,001 % or less based on the total weight of the composition.
  • the content of the vegetable oil (i) and the active substance (ii) can be 0,1- 20%, preferably 0,25-5%, more preferably 0,5-2%, based on the total weight of the composition.
  • the present invention also provides the use of the aforementioned composition in hair care compositions, preferably in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity.
  • the present invention provides the use of a composition according to the invention in skincare or haircare compositions.
  • the present invention also provides a method for preparing a chemically modified vegetable oil, said method comprising (i) a glycerolysis step comprising reacting a vegetable oil with glycerin using a lipase as catalyst, and (ii) an esterification step comprising esterification of the product of step (i) with a dicarboxylic acid.
  • the vegetable oil is selected from the group, consisting of Coconut oil, Babassu oil, Crambe oil, Pequi oil, Mango oil, Grape oil, Maracuja oil, Pumpkin Seed oil and Pracaxi oil, and/or the dicarboxylic acid is selected from the group, consisting of adipic acid and sebacic acid.
  • the present invention also provides a chemically modified vegetable oil obtained by the process described herein.
  • the present invention relates to cosmetic compositions comprising vegetable oils.
  • vegetable oils also referred to as vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are known as mixtures of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fats from seeds. Olive oil, palm oil, and rice bran oil are examples of fats from other parts of fruits. In common usage, vegetable oil may sometimes refer to vegetable fats which are liquid at room temperature. Many vegetable oils are edible.
  • the vegetable oil of the present invention can be a synthetic or naturally occurring vegetable oil. In particular, the vegetable oil according to the invention can be one or more vegetable oils.
  • a vegetable oil used in the composition of the invention may also comprise a certain amount of another vegetable oil, depending on the content specific case and the purity.
  • the vegetable oil comprises one or more vegetable oils, selected from the group consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil, Baobab oil, Rose flower oil, Comgerm oil, Walnut seed oil, Canola (Rapeseed) oil, Brazil nut oil, Baobab seed oil, Moringa Oleifera Seed Oil, Camelina sativa seed oil, Babassu nut oil, Camellia oil, Macadamia Integrifolia S.
  • vegetable oils selected from the group consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil
  • Oil Crambe oil, Manila oil, Sesame seed oil, Macadamia Temifolia S. Oil, Soybean oil, Avocado oil, Jojoba seed oil, Safflower oil, Shea butter, Argan oil, Guar oil, coconut oil, Mango oil, Pracaxi Oil, Pumpkin Seed Oil, Grape Seed Oil, Pequi Oil, Passion Fruit Oil, Amaranthus oil, Kokum oil, Cassia oil, and Sunflower oil.
  • the vegetable oil is one or more of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and coconut oil, preferably Avocado oil, Baobab oil, Guar oil, Amaranthus oil.
  • the oils can be used as supplied or can be prepared in known procedures.
  • active weight means the real weight of active, and not the total weight of product as it is. For example, the active weight of 1.5g of a given raw materials that is 80% active, in fact 1.2g.
  • the present invention is also directed toward the use of such a composition which can be used, for example, for simultaneously washing and conditioning the hair.
  • the specific surfactant combination in the specific ratio according to the invention makes it possible to achieve at the same time an acceptable compromise between the following attributes: viscosity of the composition, cleansing properties and conditioning properties, while maintaining stability.
  • the cosmetic compositions according to the invention are able to provide excellent conditioning effects such as increased hydrophobicity to the hair.
  • Fibers with higher hydrophobicity are less adhesive one towards the other. They separate more easy, which leads to a free-flowing hair which is easy to manage.
  • compositions of the invention can confer on the hair, a noteworthy treating effect which is revealed in particular by an ease of detangling, as well as a contribution on softness and shine without major feeling of greasiness.
  • the composition has a satisfactory viscosity.
  • composition having a satisfactory viscosity it is meant here a composition that has an apparent viscosity comprised between 5,000 and 12,000 cps, for instance comprised between 7,000 and 11,000 cps, for instance comprised between 8,000 and 11,000 cps, for instance comprised between 9,000 and 10,000 cps cps.
  • the apparent viscosity of each composition was as indicated in the Material and Methods section.
  • conditioning the hair or “improved conditioning” it is meant the improvement of ease of detangling and/or ease of combing, softness and/or shine.
  • Ease of detangling may be determined by the measurement of the time required for detangling the hair by using the wider teeth of a comb. The shorter the detangling time, the easier to detangle the hair is.
  • Ease of combing may be determined by the measurement of the work required for combing the hair by using the wider teeth of a comb. The lower the combing work, the easier to comb the hair is.
  • Softness, or hair feel, and shine may be assessed by an expert panel using sensorial tests on hair care on length and tips.
  • composition of the invention is a hair care composition, preferably a hair conditioning and cleansing composition, also called “cleansing conditioner”.
  • the amounts of surfactant refer to the actual amount of active surfactant compound present in the composition. In other words, it does not include the residue which may be present as an impurity in a commercially available surfactant mixture, or water when presenting in an aqueous solution.
  • the active ingredient of the cosmetic composition of the present invention is a combination of a vegetable oil (A), as noted above, and a chemically modified oil (B) as a co-active substance.
  • oil oligomers derived from triglycerides or liquid esters are (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and/or (iii) linear or branched hydrocarbons.
  • Oil oligomers derived from triglycerides can be prepared by glycerolysis as described in the Examples section.
  • the diglycerides obtained from glycerolysis can be used as active substances according to the invention.
  • Another example of chemically modified oil compounds useful in the invention is the (ii) oil based estolides.
  • Oil-based estolides as referred to herein are oligomeric esters derived from a vegetable oil, and contain special fatty acid with an additional functional group. They cover a wide range of viscosity and, by virtue of their adaptable molecule, can have product properties that vary within a spectrum of above-average width.
  • the scheme below shows the basic structure of an estolide.
  • a hydroxy-fatty acid forms the basis of the estolides which is able to form oligomers at first by self-esterification.
  • the estolide number (EN) represents the degree of oligomerization.
  • the hydroxy acids used may come from natural sources, for example. This is available as such or in its hydrogenated form.
  • a hydroxy acid may be obtained from unsaturated fatty acids using mineral acids as a catalyst.
  • the oligomerization reaction is terminated by a capping fatty acid which offers the ability to influence the product properties.
  • the resulting estolide still has a free acid group on the starting fatty acid which can be further esterified with alcohols, e.g. linear or branched alcohols.
  • the oil-based estolides (ii) as co-active substances are preferably derived from vegetable oil triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms, and/or the oil based estolides (ii) are preferably derived from lauric acid and epoxidized triglycerides polyester, lauric acid and epoxidized jojoba oil polyester, hexanoic acid and epoxidized triglycerides polyester, hexanoic acid and epoxidized jojoba oil polyester, and hexanoic acid and epoxidized jojoba oil polyester.
  • the co-active substance used in the invention is chosen from one or more of sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized Jojoba oil polyester, and hydrogenated Castor oil / hydrogenated Castor oil/Adipic Acid Copolymer / Caprylic/Capric Triglyceride.
  • a preferred co-active compound is (iii) a linear or branched hydrocarbon.
  • the hydrocarbon is one or more of liquid or solid hydrocarbons, oils or waxes, and can be selected from one or more C6-C90 straight or branched hydrocarbons.
  • the hydrocarbons can be selected from straight or branched Ce-Ceo hydrocarbons.
  • Further examples for hydrocarbons are one or more of decane, dodecane, tetradecane, distillates (Fischer-Tropsch): heavy, Cl 8-50- branched, cyclic and linear, CAS: 1262661-88-0, isooctane, squalene and squalene.
  • Dermalcare AD208® supplied by Syensqo (diethylhexyl adipate).
  • the co-active ingredient is preferably present in an amount of 0,1-20% by weight, preferably 0,5-2%, more preferably 0,5-1%, based on the total weight of the composition.
  • the co-active ingredient, or the mixture of the vegetable oil and the co-active substance (co-active ingredient) can be present in 0,1%, 0,15%, 0,20%, 0,25%, 0,30%, 0,35%, 0,40%, 0,45%, 0,50%, 0,55%, 0,60%, 0,65%, 0,70%, 0,75%, 0,80%, 0,85%, 0,90%, 0,95%, 1,00%, 1,05%, 1,10%, 1,15%, 1,20%, 1,25%, 1,30%, 1,35%, 1,40%, 1,45%, 1,50%, 1,55%, 1,60%, 1,65%, 1,70%, 1,75%, 1,80%, 1,85%, 1,90%, 1,95%, 2,00%, 2,1%, 2,2%, 2,3%, 2,4%, 2,5%, 2,6%, 2,7%, 2,8%, 2,9%, 3,0%, 3,1%, 3,
  • compositions of the invention may contain one or more silicone oils, or can be silicone oil free compositions.
  • the compositions of the invention are free of silicone oil.
  • silicone oil free compositions contain less than 0,001% by weight of silicone oil. More preferably, the compositions contain less than 0,0005%, less than 0,0001%, less than 0,00005%, less than 0,00001%, less than 0,000005%, or less than 0,000001% of silicone oil, based on the total mass of the composition.
  • the compositions contain less than 5 ppm, less than 1 ppm, less than 0,05 ppm, less than 0,01 ppm, or less than 0,001 ppm of silicone oil.
  • a parameter of the composition of the present invention which may have an influence on its properties is the active weight ratio of the vegetable oil to the coactive substance (A) / (B).
  • the weight ratio can, for instance, be 40/60, 50/50, 60/40 or 70/30.
  • the ratio is advantageously 1 : 1.
  • the active weight ratio of the vegetable oil to the co-active ingredient is 45:55, 65:45, 41 :59, 42:58; 43:57, 44:5,46:54, 47:53, 48:52, 49:51, 50:50, 51 :49, 52:48, 53:47, 54:46, 55:45, 56:44, 57:43, 58:42, 59:41, 60:40, 61 :39, 62:38, 63:37, 64:36, 65:35, 66:34, 67:33, 68:32, 69:31, or 70:30.
  • a particularly preferred range for the active weight ratio is between 40/60 to 50/50.
  • the composition can be prepared from a vegetable oil (A) and a co-active substance (B) in a mass ratio of 1 : 1, and formulated in shampoo surfactant chassis at a total concentration of 1 %.
  • active agents i.e. vegetable oil (A) and co-active substance (B)
  • preferred combinations of a vegetable oil (A) and a co-active substance (B) include combinations of one or more of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Jojoba oil, Cassia oil, Argan oil, coconut oil, Rice Bran oil, and Crambe oil, preferably Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, coconut oil, such as:
  • dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;
  • polyester dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;
  • More particularly preferable combinations are, as vegetable oils (A) Avocado oil, Baobab oil, Guar oil, Amaranthus oil, together with one or more of co-active substances (B).
  • composition preferably further comprises one or more ingredients, selected from the group, consisting of a pH regulating system, emollient(s), excipient(s), a surfactant system, guar, rheology modifier(s), antioxidant(s), conditioning polymer(s) and solubilization agent(s) as known in the art.
  • the composition can also comprise a chassis as described below.
  • a pH regulating system comprises citric acid.
  • composition of the invention can include a sulfated or sulfate-free chassis.
  • Suitable chassis are disclosed in US 2012/021025 Al, the content of which is incorporated by reference.
  • Some appropriate structured surfactant systems are described in the following documents: WO9705857, W02000059454, W001019949, WO9932069, W00170926, W00170193, WO0267892,
  • chassis compositions are provided below and in the Materials and Methods section.
  • the composition of the invention may further comprise at least one emollient, preferably a liquid fatty ester other than the coactive ingredient.
  • emollients useful in the invention include ethyl laurate, butyl laurate, hexyl laurate, isohexyl laurate, isopropyl laurate, isoamyl laurate, methyl myristate, ethyl myristate, butyl myristate, isobutyl myristate, isopropyl myristate, 2-octyldodecyl myristate, 2-ethylhexyl monococoate (or octyl monococoate), ethyl palmitate, isopropyl palmitate, isobutyl palmitate, 2-ethylhexyl palmitate (or octyl palmitate), butyl stearate, isopropyl stearate, isoprop
  • the ester is a fatty ester chosen from isoamyl laurate, isopropyl myristate, methyl myristate, ethyl myristate, butyl myristate, isobutyl myristate, 2- octyldodecyl myristate, 2-ethylhexyl monococoate (or octyl monococoate), ethyl palmitate, isopropyl palmitate, isobutyl palmitate, 2-ethylhexyl palmitate (or octyl palmitate), butyl stearate, isopropyl stearate, isobutyl stearate, isocetyl stearate, isostearyl isostearate, isopropyl isostearate, 2-ethylhexyl stearate (or octyl stearate), isononyl isononanoate
  • An emollient if present in the composition of the invention, can advantageously vary from 0.1 to 10%, preferably 0.5 to 5% by weight relative to the total weight of the composition.
  • the composition of the invention may further comprise at least one co-surfactant preferably a glycol ester of fatty acid or diacid, more preferably a glycol distearate. If present, the total amount of a co-surfactant in the composition of the invention is advantageously varying from 0.1 to 10%, preferably 0.5 to 5% by weight relative to the total weight of the composition.
  • composition of the invention may further comprise at least one emulsifier preferably an alkoxylated fatty acid or derivative thereof.
  • the emulsifier is a mono- or poly- alkyl or alkenyl ester of an alkoxylated fatty acid, with said fatty acid being a saturated or unsaturated hydroxylated (C8-C22) fatty acid, preferably a unsaturated hydroxylated (C8-C22) fatty acid.
  • saturated or unsaturated hydroxylated (C8-C22) fatty acids include ricinoleic acid, lesquerolic acid, hydroxy erucic acid (16- hydroxydocos-cis-13-enoic acid) or hydroxypalmitoleic acid (12-hydroxyhexadec- ci s-9-enoic acid), and combinations thereof.
  • Emulsifiers which may be incorporated into the composition of the invention may be obtained by esterification of alkoxylated fatty acids, which are commercially available compounds. Such reactions can be implemented by conventional methods which are well known by the skilled person.
  • Suitable emulsifiers include PEG- 18 CASTOR OIL DIOLEATE, which is an oleic acid diester of ethoxylated castor oil in which the average ethoxylation value is 18, and which is sold for instance under the name Marlowet CG.
  • PEG 16 CO Oleate available under the name Alkamuls PEG 16 CO sold by Syensqo.
  • an emulsifier is present in a concentration ranging from 0.01 to 10% by weight relative to the total weight of the composition, for example from 0.1 to 5 %, for example from 0.2 to 4 %, for example from 0.5 to 3%.
  • composition according to the invention can further comprise at least one fatty alcohol, preferably C16-C18 linear fatty alcohols.
  • the fatty alcohol can be present in an amount varying from 0.5 to 15%, preferably 1 to 10% by weight relative to the total weight of the composition.
  • the cosmetic compositions of the invention can include an antioxidant.
  • Antioxidants act as free radical acceptors and can terminate free radicals at the initiation stage.
  • Preferred antioxidants are hindered phenolics like BHA (Butylated hydroxyanisole), BHT (Butylated hydroxytoluene), TBHQ (tertiary butylhydroquinone), and tocopherols, as well as polyhydroxy phenolics like propylgallate are primary antioxidants, which delay or inhibit the initiation step by reacting with a lipid free radical or by inhibiting the propagation step by reacting with the peroxy or alkoxy radicals.
  • suitable antioxidants include, but are not limited to, phenolic substances, butylated hydroxyanisole, butylated hydroxytoluene, tertiary butylhydroquinone, tocopherols, polyhydroxy phenolics, and propyl gallate.
  • the anti oxi dant(s) may be present in an amount of 0 to 10% by weight, preferably 0 to 1% by weight more preferably 0,1 to 0,9% by weight, even more preferably 0,1 to 0,5% by weight, based on the total mass of the composition.
  • composition according to the invention can comprise a physiologically acceptable medium.
  • a physiologically acceptable medium is a medium which is particularly suitable for the application of a composition of the invention to the hair.
  • the physiologically acceptable medium is generally suited to the nature of the substrate to which the composition must be applied, and also to the way in which the composition must be packaged.
  • the composition of the present invention comprises water in an amount of from 5 to 90 % by weight relative to the total weight of the composition.
  • It may comprise for instance at least 25 %, for instance at least 50 %, for instance at least 60 % of water, relative to the total weight of the composition.
  • the cosmetically acceptable aqueous medium can be composed solely of water.
  • the composition of the invention may further comprise at least one water-miscible organic solvent.
  • the cosmetically acceptable aqueous medium can be composed of a mixture of water and of a cosmetically acceptable solvent, such as a lower C1-C4 alcohols or such as alkylene glycols.
  • a cosmetically acceptable solvent such as a lower C1-C4 alcohols or such as alkylene glycols.
  • the lower C1-C4 alcohols are preferably chosen from ethanol, isopropanol, tert-butanol, and n- butanol.
  • the alkylene glycols are preferably chosen from propylene glycol and glycol ethers.
  • composition of the invention may further comprise additional optional ingredients which may bring specific benefits for the intended use.
  • optional ingredients may include colorants, pearlescent agents, emollients, hydrating agents, preservatives and pH adjusters.
  • colorants pearlescent agents, emollients, hydrating agents, preservatives and pH adjusters.
  • composition of the present invention may further comprise from about 0.1 to about 50 % by weight, more typically from about 0.3 to about 25 % by weight, and still more typically from about 0.5 to 10 % by weight, of one or more benefit agents.
  • composition according to the present invention may optionally further comprise other ingredients common in cosmetic formulations, such as, for example, preservatives such as benzyl alcohol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium benzoate, potassium sorbate, salicylic acid, methylchloroisothiazolinone and methylisothiazolinone, thickeners such as high molecular weight crosslinked polyacrylic acid (carbomer), PEG diester of stearic acid and the like, and viscosity modifiers such as block polymers of ethylene oxide and propylene oxide, electrolytes, such as sodium chloride, sodium sulfate, and polyvinyl alcohol, pH adjusting agents such as citric acid, succinic acid, phosphoric acid, sodium hydroxide, and sodium carbonate, perfumes, dyes, and sequestering agents, such as disodium ethylenediamine tetra-acetate.
  • preservatives such as benzyl
  • hair care compositions may optionally comprise, based on 100 % by weight of the personal care composition and independently for each such ingredient, up to about 10%, preferably from 0.5 % to about 5.0 %, of such other ingredients, depending on the desired properties of the hair care composition.
  • composition according to the present invention further comprises a fragrance material or perfume.
  • the term “fragrance material or perfume” means any organic substance or composition which has a desired olfactory property and is essentially non-toxic. Such substances or compositions include all fragrance material and perfumes that are commonly used in perfumery or personal care compositions. The compounds involved may be natural, semi-synthetic or synthetic in origin.
  • the composition comprises from 0.01 to 10 % by weight of the fragrance material or perfume based on the total weight of the composition. In another embodiment, the composition comprises from 0.1 to 5 % by weight of the fragrance material or perfume based on the total weight of the composition. In still another embodiment, the composition comprises from 0.2 to 2 % by weight of the fragrance material or perfume based on the total weight of the composition.
  • a hair care composition provided by the present invention is used in a manner known in the art, for example by application of the composition to the hair and optionally rinsing the composition off of the hair with water.
  • the composition of the invention may have a pH comprised between 4 and 11, for instance between 4 and 6.
  • composition of the invention may also take the form of concentrates that are suitable to prepare a haircare product.
  • Concentrates including a mixture of surfactants and/or conditioning agents and/or solubilizer are advantageous as their use would reduce the need to transport a plurality of individual components.
  • Personal care compositions are usually prepared by mixing individual surfactants, solubilizers and conditioning agents. These components may be supplied as concentrated solutions which are diluted and/or and combined in appropriate ratios by the formulator.
  • composition of the invention may further comprise a thickener.
  • a composition of the invention may comprise less than 5 % by weight of an additional thickener.
  • a composition of the invention may comprise less than 5 % by weight of polymeric thickener(s), relative to the total weight of composition, for instance less than 3 % by weight, for instance less than 2 % by weight, for instance less than 1 % by weight.
  • a composition of the invention may comprise substantially no polymeric thickener, i.e. from 0 to less than 0.1 % by weight of polymeric thickener per 100 % by weight of the composition, for instance no polymeric thickener, i.e. 0 % by weight of polymeric thickener per 100 % by weight of the composition.
  • stabilizers such as crosslinked acrylic polymers of the Carbopol type are frequently used.
  • these stabilizers can have the drawback of reducing the cosmetic performance. For instance, in the case of shampoos, using such synthetic polymers makes the hair more laden (charged or loaded) and coarser.
  • a composition of the invention may comprise less than 5 % by weight of one crosslinked copolymer.
  • a particularly preferable formulation according to the invention comprises the following:
  • a further example for a cosmetic formulation in the form of an emulsion is as follows:
  • the above formulation is particularly suitable for conditioner, mask, serum, combing cream, cowash, lotion, or a prewash.
  • the present invention also provides a method for preparing a chemically modified vegetable oil, said method comprising (i) a glycerolysis step comprising reacting a vegetable oil with glycerin using a lipase as catalyst, and (ii) an esterification step comprising esterification of the product of step (i) with a dicarboxylic acid.
  • step (i) is carried out by the reaction between triglyceride and glycerin, in stoichiometry for the majority formation of di glycerides, such that monoglycerides will be formed in smaller quantities, using lipases as a catalyst.
  • any of the vegetable oils described herein, which is mostly comprised of triglyerides is treated with glycerin in a glycerolysis using a lipase as a catalyst.
  • step (ii) the vegetable oil(s) subjected to glycerolysis is esterified with a dicarboxylic acid.
  • Suitable dicarboxylic acids are selected from dicarboxylic acids of the general formula:
  • Y is preferably a saturated or unsaturated alkyl chain, or Y is an aromatic residue.
  • Y can be a divalent 1,2- 1,3 or 1,4-phenyl residue. More preferably, the dicarboxylic acid is of the general formula
  • Y is -(CFbjn- wherein n is preferably 1-20 or 1-10, more preferably, n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
  • Particularly preferred dicarboxylic acids are oxalic acid (ethanedioic acid), malonic acid (propanedioic acid), Succinic acid (butanedioic acid), Glutaric acid (pentanedioic acid), adipic acid (hexanedioic acid), pimelic acid (heptanedioic acid), suberic acid (octanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), phthalic acid (benzene- 1,2-dicarboxylic acid), orthophthalic acid, isophthalic acid (benzene- 1,3 -dicarboxylic acid), metaphthalic acid,
  • the vegetable oil subjected to step (i) is selected from the group, consisting of Coconut oil, Babassu oil, Crambe oil, Pequi oil, Mango oil, Grape oil, Maracuja oil, Pumpkin Seed oil and Pracaxi oil, and/or the dicarboxylic acid is selected from the group, consisting of adipic acid and sebacic acid.
  • the lipase used in step (i) is commercially available lipase as supplied from Novozymes, for example NZ 435TM or Lipura FlexTM.
  • a typical lipase loading is about 3-8% by mass or 3-6% by mass.
  • lipase loading is 4,5% by mass.
  • a suitable ratio of glycerine to vegetable oil is 2: 1 or 3: 1 in terms of moles.
  • 1 mol of vegetable oil (triglyceride) is reacted with 2 mol of glycerin.
  • the temperature is preferably increased.
  • a generally preferable increased temperature range for step (ii) is 150-250°C, preferably 170-200°C.
  • a suitable temperature increase rate is 5°C/h, preferably 10°C/h, more preferably 15°C/h.
  • the product of step (i) is not isolated for step (ii), but is used as obtained from step 1, with the mixture of mono- and diglycerides to start step (ii) of esterification with the chosen diacid.
  • the vegetable oil, 14 part of glycerine, and lipase is loaded in a glass reactor, and homogenized using mechanical agitation.
  • the proportion considered between triglyceride and total glycerin for the glycerolysis reaction, predicting higher final levels of diglyceride, will be 1 mol of triglyceride for 2 mol of glycerin.
  • the temperature increases to 65-70oC, Nitrogen is adopted to the inert atmosphere.
  • the monoglyceride, diglyceride contents and hydroxyl index will be controlled to complete the glycerolysis reaction.
  • stage 1 The product of stage 1 is loaded in a glass reactor, the dicarboxylic acid added homogenized using mechanical agitation, Nitrogen is adopted to inert atmosphere.
  • the temperature is increased to 150-230°C, preferably 170°C to 200°C with a temperature increase rate of 10°C per hour.
  • the reaction is accompanied by a reduction in the acid number.
  • di glyceryl esters and monoglyceryl esters can be obtained according to the following schemes: a) formation of diglyceryl ester
  • the molecules represent an oleic acid triglyceride (generic oil), tri glyceryl oleate, however it should be noted that the above example is a generic representation, the fatty acids in the structure of the triglyceride and subsequently in the structure of the diglyceride and monoglyceride products will be those derived from the oil used in the reaction, which can be, for example, from C8 to C22 or higher, and can be saturated, unsaturated and polyunsaturated chains.
  • the polymerization of the diacid is possible, forming other molecules in addition to the main ones.
  • the present invention also provides a chemically modified vegetable oil obtained by the aforementioned process.
  • the cosmetic compositions of the invention can be used in different cosmetic applications, in particular haircare and skincare.
  • a skincare composition can be formulated within a wide range of pH levels.
  • the pH of the topical composition ranges from 1.0 to 13.0.
  • the pH of the topical composition ranges from 2.0 to 12.0.
  • Other pH ranges suitable for the subject composition include from 3.5 to 7.0, or from 7.0 to 10.5.
  • Suitable pH adjusters such as sodium hydroxide, citric acid and triethanolamine may be added to bring the pH within the desired range.
  • a cosmetic skincare composition may comprise additional cosmetic ingredients. These components may be considered active ingredients or inactive ingredients, and can be categorized by the benefit they provide or by their postulated mode of action; however, it is to be understood that the additional components can in some instances provide more than one benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit the agent to that particular application or applications listed.
  • cosmetic ingredient classes include: organic solvents, silicones, pH adjusters, chelating agents, gelling agents, proteins, vitamins, emollients, oils, hydroxy acids, exfoliants, retinoids, viscosity modifiers, polymers, minerals, insect repellents, lubricants, preservatives, botanicals, clarifying agents, humectants, non-biological surfactants, antioxidants, thickeners, softeners, sunscreens, moisturizers, dyes, colorants, fragrances, abrasives, absorbents, aesthetic components such as essential oils, skin sensates, astringents, anti-acne agents, anti-caking agents, antifoaming agents, antimicrobial agents, depigmenting agents, anti-inflammatory agents, advanced glycation end-product (AGE) inhibitors, steroids, binders, biological additives, buffering agents, bulking agents, chelating agents, chemical additives, denaturants, external analgesics, keratolytic agents, des
  • compositions of the present invention can be used in personal care products.
  • the compositions can be used by applying the cosmetic composition to an area of skin on a body; washing the area of skin on the body; and rinsing the area of skin on the body.
  • a topical cosmetic composition can be formulated as, for example, a suspension, emulsion, nanoemulsion, hydrogel, multiphase solution, liposomal dispersion, lotion, cream, gel, foam, ointment, paste, spray, conditioner, shampoo, mask, cleanser, micellar water, tonic, makeup (e.g., lipstick, foundation, bronzer, rouge, eyeshadow), and/or after-shave.
  • the cosmetic composition of the invention can be used for improving the health and/or appearance of skin wherein a topical cosmetic composition is applied directly to an area of the subject’s skin in need thereof.
  • compositions of the invention are preferably used in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity.
  • the compositions of the invention are effective in haircare.
  • the compositions are effective in hydrophobicizing the hair.
  • the cosmetic composition of the invention is useful in haircare products such as shampoo or conditioning products. Namely, using compositions of the invention, hair fibers treated with the mixtures become more hydrophobic in comparison with the fibers treated with individual components. There are also indications that the deposition of oil on the fibers is facilitated by the presence of co-active. This effect of the two actives with respect to their surface properties (more pronounced hydrophobicity) correlated with improved performance in sensorial tests. Also, it is possible to use the haircare compositions provided by the invention for improved surface properties.
  • the mixture of a vegetable oil and a coactive substance can also be used as silicone oil free alternatives for hair conditioners in hair care products.
  • compositions of the present invention are useful for skincare applications, such as emollient compositions, skin moisturizing compositions and other skincare applications such as skin masks, anti-ageing applications and similar applications.
  • Two different compositions can be achieved using different methods to obtain higher levels of diglycerides from triglycerides using enzymes as catalysts. It is possible to obtain a mixture of diglycerides, monoglycerides and fatty acids removed from the triglyceride structure through the enzymatic hydrolysis procedure, or monoglycerides and diglycerides without the presence of free fatty acid, by glycerolysis reaction also using lipases as catalysts in the process.
  • Vegetable oil with triglyceride content e.g. Coconut Oil, Babassu Oil, Crambe Oil, Pequi Oil, Mango Oil, Grape Oil, Maracuja Oil, Pumpkin Seed Oil or Pracaxi Oil.
  • Lipase e.g. NZ 435 or Lipura Flex enzyme (lipase B from Candida Antarctica), supplied by Novozymes
  • the triglyceride water and lipase are loaded in a glass reactor;
  • the reactor is heating using water to 65-70°C of temperature
  • Vegetable oil with triglyceride content e.g. Coconut Oil, Babassu Oil, Crambe Oil, Pequi Oil, Mango Oil, Grape Oil, Maracuja Oil, Pumpkin Seed Oil or Pracaxi Oil.
  • Lipases e.g. NZ 435, Lipura Flex (lipases B from Candida antarctica), supplied by Novozymes
  • the triglyceride, 1/4- 1/2 part of glycerin by mole, and the lipase is loaded in a glass reactor, homogenized using mechanical agitation.
  • the amount of glycerin is divided into 4 parts which is added consecutively to the reaction.
  • the temperature increases to 65-70°C, and mechanical stirring is performed for homogenization and reaction.
  • the remainder of the glycerin is added every 12 hours.
  • Chemical enzymatic transformation As described above, chemical-enzymatic transformation involving two reaction stages was used. In the first step, different vegetable oils will react with glycerin, in a glycerolysis process, to form diglycerides and monoglycerides. In a second step they are esterified with a dicarboxylic acid such as adipic or sebacic acid.
  • a dicarboxylic acid such as adipic or sebacic acid.
  • Vegetable oil with triglyceride content e.g. coconut Oil, Babassu Oil, Crambe
  • Oil - Pequi Oil, Mango Oil, Grape Oil, Maracuja Oil, Pumpkin Seed Oil or Pracaxi Oil.
  • the triglyceride, 1/4-1/2 part of glycerine by mole, and the lipase is loaded in a glass reactor, homogenized using mechanical agitation.
  • the amount of glycerin is added in 4 parts to the reaction.
  • the temperature increases to 65-70°C, Nitrogen is adopted to generate an inert atmosphere.
  • the monoglyceride, diglyceride contents and hydroxyl index are controlled to complete the glycerolysis reaction.
  • the reaction times are: 1st, 2nd and 3rd stage - 4 to 8 hours of reaction after adding glycerin, preferably 6 hours, 4th stage - 12 -18 hours of reaction after adding glycerin, preferably 14 hours.
  • stage 1 The product of stage 1 is loaded in a glass reactor, the dicarboxylic acid added homogenized using mechanical agitation, nitrogen is adopted to maintain an inert atmosphere.
  • the temperature is increased to 170°C to 200°C, increasing at a rate of 10°C per hour.
  • the reaction is accompanied by a reduction in the acid number to values below 1.0 mg KOH/g.
  • the reaction time for the esterification step is 6 to 12 hours, more preferably 8 hours.
  • the reaction was conducted under an inert nitrogen atmosphere.
  • a threenecked round-bottom flask of 250 mL, equipped with a magnetic stirrer, a condenser, a thermal probe, and a magnetic stirrer 90 g of avocado oil (0.104 mol), 11.86 g of acetic acid (0.207 mol) and 32.29 g of Amberlite 120H IR were introduced.
  • the mixture was stirred and heated to 75 °C with an oil bath. When the temperature reached 75 °C, 35 mL of an aqueous solution of H2O230% was slowly added into the mixture using a syringe driver over one hour while maintaining the temperature at 75 °C.
  • the reaction was conducted under an inert nitrogen atmosphere.
  • a three-neck round-bottom flask of 250 ml, equipped with a magnetic stirrer, a condenser, a dropping funnel and a temperature probe were added 9.74 g of sebacic acid (0.058 mol).
  • the mixture was heated at 150 °C and 30 g of Epoxidized Jojoba oil (0.049 mol) were added with the dropping funnel over lh30. When the introduction was completed, the mixture was stirred at 150 °C for lh30. The mixture was allowed to cool down at room temperature to recover the final product as a yellowish grease solid.
  • the contact angle was measured as an indication of the degree of hydrophobicity.
  • Different formulations of vegetable oil (A) and co-active substance (B) were tested to measure the contact angle. The measurement was performed as indicated in the Material and Methods section.
  • Figure 1 shows the results.
  • the hydrophobicity is improved with the specific combination of vegetable oil (A) and co-active substance (B) according to the invention. This parameter makes it possible to determine the condition of the hair and also to observe whether there is a deposit of active ingredients.
  • DV920 Hydrogenated castor oil and hydrogenated castor oil/adipic acid copolymer and caprylic/capric triglyceride (available from Syensqo).
  • the cosmetic composition of the invention has a strong potential for effective cosmetic composition in particular in hair conditioning, and also as silicone oil-free products in hair care products.
  • Section 1 presents information on the components used in the examples. That includes the actives of interest (with potential conditioning action) and the surfactants or other components employed in the surfactant chassis of a particular active.
  • Section 2 the experimental protocols are described, employed to prepare the formulations, perform the in vitro (wet and dry combing) and in vivo evaluations.
  • Table 2 presents the composition of surfactant chassis of the formulation used in the examples.
  • Table 1 Components used to prepare the formulations. Table 2. Composition of surfactant chassis of the formulation, oil-infused shampoo.
  • Section 2.1 presents the protocols for the preparation of the studied formulation.
  • Section 2.2 explains the protocol for production of home bleached tresses, starting from virgin tresses.
  • sections 2.3-2.5 the protocols for characterization of the formulation are described: transmittance, viscosity and stability, respectively.
  • sections 2.6 and 2.7 the procedure for evaluation of the systems is described in combing test - wet and dry mode, respectively.
  • Section 2.8 presents the procedure, used for evaluation of the humidity of the tresses.
  • the protocol for measurement of contact angle of water on hair fibers is described, and section 2.10 explains how the deposit of active on the hair fiber is quantified.
  • section 2.11 it is explained how the products are evaluated in sensorial panels.
  • the procedure for the preparation of shampoo formulation is as follows.
  • the 2 blends (Oil blend and Surfactant thickening blend) were prepared during the main formulation stirring time and added to the main formulation accordingly.
  • Tresses 25 of 4 g virgin medium brown DA 450 163 8300
  • niMixTURE (/g of hair) 4.75g weigh first powder with a mask and premix with a spatula and use the add oxidant cream on top in a 600ml mixer when adding water slowly in 4 beak minutes.
  • Second step mass again each strand more deeply (25s/tress from the top to the bottom).
  • the application time must not exceed 20 min to stay significantly lower than the exposition time.
  • the transmittance of the formulations and the oils was measured via the following procedure. (1) Fill % of the cuvette (over the line) with a formulation sample.
  • the viscosity of the formulations was measured via the following procedure.
  • Formulation is filled (90%) into a 100 mL glass bottle.
  • the viscosity of the vegetable oils was measured via the following procedure.
  • the force and the work for combing are a function of the following properties/parameters (at the same speed):
  • the procedure consists of three steps: (1) Tress pre-treatment; (2) Treatment of the tress with shampoo; (3) Combing test. Below each of these steps are described.
  • the tresses were subjected to a coming test (speed of combing 300 mm/min) via a comb with narrow teeth (11 teeth per centimeter). At least 10 passes were applied. The average initial total work for combing is calculated (JEBEFORE).
  • the tresses were subjected to a coming test (speed of combing 300 mm/min) via a comb with narrow teeth (11 teeth per centimeter). At least 10 passes were applied. The average total work for combing is calculated (JTAFTER).
  • thermo gravimetric balance Producer: Mettler Toledo; model: HX204. This equipment allows real-time measurement of the mass of a sample during heating.
  • the measurement protocol is described in detail in Appendix A.
  • the contact angle on treated hair fibers was measured via tensiometer Kruss K14.
  • the tresses used in this case are home bleached. As shown in ref. 6 the home bleached tresses allow for better reproducibility and therefore clearer evaluation of the experimental trends.
  • the fiber is cut 5 cm from the root.
  • the radius of the fiber is measured via a micrometer.
  • the fiber is dipped in water container with the cuticles directed toward the end of the tip of the fiber placed in the container.
  • the instrument measures the downward force, F, exerted on the fiber via a sensitive force sensor, and calculates the contact angle from the following expression:
  • F Z ycos(0A) (2)
  • F is the force exerted by the capillary force on the fiber
  • L is the perimeter of the wetted hair fiber, calculated form the radius R of the hair fiber
  • 0A is advancing contact angle. This measurement is performed for 10 hair fibers. The outliers of the measurement are removed via the following procedure in Microsoft Excel:
  • Quartile is a type of quantile which divides the number of data points into four parts, or quarters, of more-or-less equal size.
  • the data must be ordered from smallest to largest to compute quartiles; as such, quartiles are a form of order statistic.
  • the three main quartiles are as follows:
  • the first quartile (QI) is defined as the middle number between the smallest number (minimum) and the value that falls between the 25th and 75th percentiles of the sample (which cuts off the first quarter of all the samples). It is also known as the lower quartile, as 25% of the data is below this point.
  • the second quartile (Q2) is the median of a data set; thus 50% of the data lies below this point.
  • the third quartile (Q3) is the middle value between the value that cuts off the last quarter of samples and the highest value (maximum) of the data set. It is known as the upper quartile, as 75% of the data lies below this point.
  • the fraction of the deposited actives (oil or DV920) on the tresses was measured.
  • the actives were extracted from the treated tresses via organic solvent. After that the obtained solution was analyzed via liquid chromatography (triglyceride) or gas chromatography (DV920).
  • the concentration of the respective active in the solution was calculated with the help of a calibration curve for the respective active, build prior to the experiment. This information was then used to calculate the mass fraction of the active deposited on the tress; more precisely the fraction of total active, present in the formulation, which remained on the tress.
  • the procedure is described in detail in Appendix B. 2.11. Sensorial panels in hairdresser’s saloon (shampoo formulations).
  • the shampoo is rinsed off from the hair in the following sequence: (1) 30 seconds, right side; (2) 30 seconds, left side; (3) 45 seconds, right side; (4) 45 seconds, left side.
  • the sensorial perception of the hair is evaluated with respect to the following parameters:
  • compositions and methods are described in terms of “comprising,” “containing,” or “including” various components or steps, the compositions and methods can also “consist essentially of or “consist of the various components, substances and steps. As used herein the term “consisting essentially of shall be construed to mean including the listed components, substances or steps and such additional components, substances or steps which do not materially affect the basic and novel properties of the composition or method.
  • a composition in accordance with embodiments of the present disclosure that "consists essentially of the recited components or substances does not include any additional components or substances that alter the basic and novel properties of the composition. If there is any conflict in the usages of a word or term in this specification and one or more patent or other documents that may be incorporated herein by reference, the definitions that are consistent with this specification should be adopted.

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Abstract

La présente invention concerne des compositions cosmétiques, en particulier des compositions de soins capillaires ou de soins cutanés. L'invention concerne également l'utilisation et des procédés d'utilisation de telles compositions, en particulier des compositions de soins capillaires ou de conditionnement capillaire ou des compositions de soins cutanés à base d'huiles végétales et d'une substance co-active.
PCT/EP2025/057575 2024-03-20 2025-03-20 Compositions cosmétiques, leur utilisation et procédés d'utilisation de telles compositions Pending WO2025196161A2 (fr)

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WO1999032069A2 (fr) 1997-12-18 1999-07-01 Unilever Plc Composition liquide avec une stabilite amelioree a basse temperature
WO2000059454A1 (fr) 1999-04-05 2000-10-12 Unilever Plc Composition liquide a stabilite amelioree dans des conditions de basse temperature
WO2001019949A1 (fr) 1999-09-16 2001-03-22 Unilever Plc Composition liquide demaquillante comprenant une phase lamellaire pourvue d'une teneur en sel faible
WO2001070926A1 (fr) 2000-03-20 2001-09-27 Unilever Plc Composition a phases multiples extrudable comprenant, dans chaque phase, un agent structurant inducteur de phase lamellaire
WO2001070193A2 (fr) 2000-03-20 2001-09-27 Unilever Plc Composition multiphase extrudable comprenant une phase lamellaire et une phase isotrope
WO2002005758A2 (fr) 2000-07-14 2002-01-24 Johnson & Johnson Consumer Companies, Inc. Gel nettoyant auto-moussant
WO2002067892A2 (fr) 2001-02-28 2002-09-06 Unilever Plc Procede de production de liquides hydratants doux contenant de grosses gouttelettes d'huile
WO2003017968A2 (fr) 2001-08-24 2003-03-06 Unilever Plc Composition demaquillante lamellaire post moussante et systeme distributeur
WO2003055455A1 (fr) 2001-12-21 2003-07-10 Rhodia Inc. Compositions stables associant des tensioactifs cationiques et des tensioactifs anioniques
WO2003055456A1 (fr) 2001-12-21 2003-07-10 Rhodia Inc. Compositions de tensioactifs stables pour suspension de composants
WO2005063174A1 (fr) 2003-12-23 2005-07-14 Unilever Plc Composition de nettoyage cristalline de liquide ordonnee a suspension d'air
WO2005084614A1 (fr) 2004-02-27 2005-09-15 The Procter & Gamble Company Composition douce pour le lavage du corps
WO2005110355A2 (fr) 2004-05-19 2005-11-24 Unilever Plc Produits nettoyants liquides personnels contenant une association d'acide gras et d'un systeme structurant a l'amidon hydrosoluble ou hydrodilatable
WO2006023548A2 (fr) 2004-08-17 2006-03-02 Rhodia Inc. Compositions tensioactives structurees a ph faible
WO2006127394A2 (fr) 2005-05-20 2006-11-30 Rhodia Inc. Compositions tensioactives structurees
WO2006135627A2 (fr) 2005-06-10 2006-12-21 Merck & Co., Inc. Inhibiteurs de l'activite akt
WO2008039440A1 (fr) 2006-09-26 2008-04-03 Rhodia Inc. Système tensioactif structuré
US20080153730A1 (en) 2006-12-20 2008-06-26 Conopco, Inc. D/B/A Unilever Stable liquid cleansing compositions comprising fatty acyl isethionate surfactant products with high fatty acid content
US20080233061A1 (en) 2007-03-23 2008-09-25 Ericka Gates Structured surfactant compositions
US20120021025A1 (en) 2009-02-05 2012-01-26 Rhodia Operations Aqueous composition suitable as shampoo

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